I just have to chime in on the clothes!
I delivered in the hospital and really didn't think much about what to wear. I labored in a big maternity tee shirt, a nursing bra, and a pair of yoga pants. I got to the hospital between 8 and 9 cm, so they didn't even really have time to offer me a gown. I probably would have refused anyhow. I just took off the pants and my undies and pushed the baby out. It worked nicely for me, as by that time I really couldn't have cared less about modesty, etc. I was ready to push, and pushing was literally the only thing I could focus on. Afterward I was able to just sit on all the absorbent padding with a sheet up to my waist - easy and comfy.
This time I'm delivering at home, but expect to be wearing much the same thing. Unless I use the birthing tub, in which case I'll probably ditch the tee shirt...
As for nursing wear, I've actually found some of it very useful. As Willo said, it's not really necessary when you're at home, but for me it was very necessary for public nursing. I never seemed to be able to cover myself well enough to feel comfortable in regular clothes unless they were *way* too big. I felt unattractive enough without wearing oversized clothing to boot!
In the very early weeks it was all frustrating. But that was mainly because of extreme engorgement and inexperience. I didn't just leak, I was a veritable fountain at all times. Even the lansinoh disposable pads didn't hold me for more than an hour at a time. By 5 weeks or so I had slowed to a constant drip, which could be managed with cloth pads if I changed them every 45 minutes or so. At that point I'd also found some comfortable nursing positions that worked for us and was able to select nursingwear that suited both my physique and nursing needs.
Nursing jammies are something of a luxury, unless you want to sleep without a bra. Leaky as I was, I needed something tight enough to hold my nursing pads in place, and that meant sleeping in my nursing bras or wearing nursing pajamas. Happily, I had some fairly comfy nursing bras, so I just slept in them most of the time. The bravado bras were fantastic for that. For nursing jammies, unless you will be nurisng in your pajamas in public, I prefer a tight cris-cross top that you just pull aside to expose your whole breast. It's so much easier that way! The majamas pj's are like that. (Though they're shaped correctly to hold the nursing pads in place, they're not actually tight enough to provide support like a bra, so I don't think they inhibit milk production.) I only have one pair, and I actually didn't buy them until I got pregnant this time around, but they are fantastic! I know they cost an arm and a leg, but I'm even thinking about getting a second pair so I can wear them all the time with this new babe.
I found that basically none of the double layered tee shirts worked for me. The under layer never seemed to stay tucked, and the openings were never in the right place. The two styles that work best for me are the tanks with the clips on the straps (like glamourmom) and those with a double layer only at the top (like majamas) both of which have an underlayer with a smaller opening (maybe 2.5" diameter) which stays positioned around your nipple the whole time you're wearing the garment. I wear the tanks with nursing pads and no bra. The majamas types I wear with a nursing bra underneath as they don't provide much if any support.